


Dalliancing Dean has a Dilemma

by krysnel_nicavis



Series: Porn on the Cutting Room Floor (and other places) [4]
Category: Supernatural
Genre: Alternate Universe - Gender Changes, Atypical Genderswap, Castiel/Dean Winchester First Time, Cunnilingus, Cused Dean Winchester, Dean Has a Vagina, Episode: s09e03 I'm No Angel, F/M, Jealous Dean, M/M, Newly Human Castiel, Porn With Plot, Porn with Feelings, Vaginal Sex
Language: English
Status: Completed
Published: 2018-02-25
Updated: 2018-02-25
Packaged: 2019-03-23 20:04:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13795287
Author URL: https://archiveofourown.org/users/krysnel_nicavis/pseuds/krysnel_nicavis
Summary: Dean gets cursed by an Angel. Or his junk does. And now he has a bit of a problem. An itch. An itch that needs scratching.Cas can help. Casdoeshelp.And Dean istotallynot jealous of anything. Maybe. Shut up.





	Dalliancing Dean has a Dilemma

**Author's Note:**

> Dalliance. Noun.:  
> an act of dallying: such as  
>  **a** : play; especially : amorous play

Dean sighed, low and rumbling. More of a growl really. He scrubbed his face with his hands in frustration before slamming the book in front of him shut. “I need a break,” he announced, chair scraping loudly on the floor as he stood.

”Okay.”

He ignored Sam’s sad puppy look, having seen it a little too much in the past couple days. Kevin briefly shot him an irritated look and a small part of him felt bad. The kid was slaving over the Demon Tablet and, quite frankly, looked like hammered shit. Might be time to toss him in the shower and stuff a burrito in his mouth. No use letting him streamline coffee and pills again. Most of him, however, couldn’t care less at the shade being thrown his way. He was tapped out of patience as it was and had none to spare for being considerate at the moment.

And that hot, tight sensation in his groin was beyond distracting. The press of it against the chair seat only helped make it worse. He snagged a beer out of the fridge, tossing the cap in the sink with another low growl. The cold liquid was a small comfort as he downed his beer.

He placed the bottle in the recycling and decided to detail Baby’s engine. He made it to the doorway before grumbling, turning back, plucking the bottle cap out of the sink, and properly disposing of it.

His beloved car helped distract him from the situation in his pants. Well, mostly. The slick, wet feeling that now accompanied the tightness made itself known every time he shifted his legs a certain way — especially so when he sat down to clean a part. Despite knowing by now that squirming in his seat wouldn’t help alleviate the sensations, he still tried to find a position that was a little more comfortable. He huffed, squirming some more when he found himself pressing down into his seat again.

Fuck. He was so _horny_.

Putting the engine part aside, he thumped his forehead on the table and cursed the dickbag Angel who had done this to him. Normally he could just rub one off and be done with it for more than a few hours. But this…

After putting out an open prayer for help with Sam after failing to shut the Gates of Hell, one of the Angels who attacked him instead in search of Castiel apparently decided that swapping out his dick for a cunt was funny, or something. At first, once the adrenaline wore off enough for Dean to notice exactly what felt different, he’d thought it was kind of fun — and that first night had, indeed, been fun experimenting with his new body. But, the longer he remained gender-swapped the more frustrated he became. And it wasn’t because there was currently no way to reverse it — Ezekiel, the Angel currently riding shotgun inside Sam, wasn’t strong enough to attempt a reversal and it wasn’t his “area of expertise”. Since waking up this morning, his womanly bits were in a constant state of arousal.

He was completely sure of one thing at the moment: he was no longer jealous of a woman’s ability to experience multiple orgasms. Fuck… His wrist hadn’t hurt this much since he was a teenager and was rubbing his dick raw.

He shifted his hips and cursed as a small rush of fluid had his boxers sticking to him. He sighed one more time and stood. May as well make of the best of it and enjoy another orgasm.

* * *

Dean was absolutely _not_ jealous

No, really. He wasn’t. He was proud of his buddy. Of course he was. Sure, the guy needed to learn how to practice safe sex, but Dean’d explain it to him later.

And he certainly _wasn’t_ jealous that some reaper bitch had managed to coerce his friend into losing his v-card. Why would he be jealous of that? This was an important milestone in Cas’ _practical_ education in humanity — he was finally getting the chance to put all that theoretical knowledge to good use. Dean may have thoroughly enjoyed killing that bitch after she’d stabbed the (former) Angel with his own Angel Blade, but the fact that _she’d_ been Cas’ first time had nothing to do with him wishing he’d killed her slower _now_. Cause it didn’t.

He focused on the engine in front of him. He hadn’t completely finished detailing it before going to pick up Cas. He’d decided to do so now. It didn’t have anything to do with Castiel admitting to having sex with whatever her name was. And he _hadn’t_ immediately stormed off to the garage immediately after the guy had admitted to only having his Angel Blade for protection. That would be stupid. He focused solely on the engine, ignoring the way his entire body flooded with a familiar heat. And especially ignoring how it had begun heating up when he’d happened to glance at Cas’ bare torso after Ezekiel had revived him, becoming a constant thrum on the ride back to the bunker — _not_ because Cas was in the back seat…

Dean shook his head, blinking at his hands. What had he been doing exactly? He studied the engine.

”Dean,” the familiar gravelly voice of the (former) Angel he’d definitely _not_ been thinking of and was definitely _not_ imagining half dressed in Baby’s back seat. “Are there any more of those burritos?”

Heat radiated through him and his heartbeat sped up. He cleared his throat and turned around. Damn. Were his eyes always that blue? “Uh, h-hey, Cas…” He leaned back against the car, fiddling with the tool in his hands. He hoped in vain that his face wasn’t red.

Castiel frowned, tilting his head. “Are you alright, Dean? You look flushed.” He made an aborted move to touch Dean’s face with two fingers. The embarrassed shame on his face made something in Dean’s chest crack.

”I’m fine, Cas,” he replied and straightened, putting the tool to the side and approaching his friend. He hated seeing that look on the man’s face. Cas should never have that expression.

He was acutely aware of Cas’ body heat. When did they get so close to each other? His breath hitched as he took in the man’s facial features. There was more stubble than he was used to. He took a shuddering breath as he realized how wet his cunt was. The way his clit felt… if he had his normal junk, his cock would be completely hard right now. “Cas…”

He watched Cas’ eyes study him, heart thudding in his chest. He saw the exact moment when realization dawned. Cas knew. He _knew_ what Dean definitely _wasn’t_ in the mood for… except, he totally _was_. He could barely admit it to himself because he was so chickenshit about it, but he was normally able to manage his physical responses to being so close to Cas better. He knew how to control his body when he had a dick. But this new anatomy… the way his arousal felt… it was confusing and he couldn’t control it. Couldn’t stop it.

It raged through his veins, a wildfire he was ill equipped to temper let alone control. He stepped closer to the other man’s warmth, body so keyed up with need his brain didn’t know what to focus on.

”Dean.”

”Cas, I…” Dean stopped at the unsure confusion in those blue eyes that always managed to lock him into place. What was he doing? Cas was his friend. His buddy. The guy was confused enough with having to deal with being human. And his tryst the night before with that bitch… who _used_ him… Unbidden, a vision of a different Cas, one who was also scruffy-faced and human… talking about bathing and orgies… The jealousy that was definitely there ramped up. He swallowed. “I…”

The confusion melted away, understanding taking its place. “Dean.”

He jumped, feeling the other’s hands on his. Larger than he was accustomed to. Instinctually, he held on, pulling Castiel closer. Just shy of pressing them together.

The lips pressing against his were warm and chapped. Stubble scratched against his face. It wasn’t awe inspiring. There were no fireworks and there wasn’t a swell of music like on TV and in movies. It wasn’t Earth shattering. But if his brain could have an orgasm, it was having one now. His cunt contracted in anticipation. The knowledge that what he wanted, what he _needed_ , inside him was so close had him feeling so hot and wet he wouldn’t be surprised if there was a visible spot on his jeans.

Cas’ body pressed flush against his. He felt himself twitch as Cas’ half-mast erection bumped against him. It was Dean’s turn to be embarrassed and unsure. He moved back, suddenly self-conscious.

”Dean? What—” Cas looked searchingly at him. Dammit. Why’d he have to look so adorable when he tilted his head? “What’s wrong?”

”Wrong?” Dean scoffed and tried to brush it off. “N-nothing’s wrong. Why would something be wrong?” Even he could hear how unconvincing he sounded.

Cas pulled away and Dean immediately missed the press of his body. “I’m pushing you. I apologize. I assumed—”

Dean grabbed Castiel’s wrist as he turned away. “Cas, wait.” Those too blue eyes turned back to him, guarded. He gulped and simply stared back. Was he really going to do this? Could he?

Cas’ expression closed off and, in response, he felt his hesitation flee in the face of panic.

”I was cursed. I-I mean I _got_ cursed. Or my junk did.” Cas paused, a hint of resignation in his eyes, then concern, then more confusion.

“I don’t—”

Dean let his wrist go. With shaky hands he undid the front of his jeans. Taking a steadying breath, he reached for Cas’ wrist again. He turned his body to the side, drew in one more breath, and guided Cas’ hand to rest on his abdomen. Slowly, he encouraged the man to slide his hand down beneath the waistband of his boxers.

Castiel’s sharp gasp sounded in his ear when his hand slid over the patch of thick hair, his middle finger slipping into the folds of his heated cunt. He gasped and held onto Cas’ arm to prevent him from pulling away again.

He needn’t have bothered. Castiel’s fingers experimentally ran along his outer folds. When Cas’ finger slipped in deeper, sliding against his hardened clit, he drew in a ragged breath. “C-Cas…” he breathed. His inner walls contracted again and he angled his hips, pressing back against the questing fingers. Cas moved to stand behind him, pressed into his back as he added another finger along side the first and continued to rub against his aching clit, free hand coming around to rest on his stomach.

Dean dropped his head back to rest on Cas’ shoulder, clinging to his arm. He grunted when the friction became rough, biting back a groan when Castiel’s hand slid lower and his fingers pushed in deeper, finding their way into his soaked opening. The fingers thrust in shallowly, coating in the slick natural lubricant Dean’s body was producing. He sighed when they pulled back and resumed stimulating his clit, sliding easily along his skin.

Dean’s free hand tangled in Cas’ thick hair. He moaned, head falling to the side and exposing his neck as the brunet mouthed along the exposed area. His heart thudded in his chest, a sheen of sweat along his brow. _H-holy fuck…_ How did he find out to do _that?_ Castiel’s fingertips swirled around his clit. He rocked his pelvis against the pressure, needing more. Needing…

“C-Cas… _please_ …”

He felt Cas’ hot breath on his hear. “You want me inside you… _Dean?_ ” His normally gravelly voice lowered further, he practically purring. The drag of his tongue up Dean’s neck made him tremble. “Do you want my thick, hot cock fucking into your dripping cunt?”

Dean moaned. “Fuck, Cas. Did you learn to talk like that from the pizza man too?”

“No.” His voice rumbled, low. “I just know exactly what I want to do with you.”

“Fucking hell…” He turned in Cas’ arms, pulling the man into a filthy, porn-worthy kiss and moaning like an experienced whore.

Castiel trailed messy wet kisses down his jaw and neck. “Would you like that, Dean?” Dean could feel the unmistakable shape of his hard cock through two layers of denim as they rutted against each other. Cas grabbed his ass with both hands and lifted him up. The sound of the Impala’s hood slamming shut echoed in the garage before Dean was lowered onto it.

“Oh, fuck, Cas. Yes,” he breathed. “God, yes. I want you.” They continued, dry humping like teenagers. “I want you. _Cas._ I want you to fuck me so bad!” Cas kissed him noisily before pulling his jeans and boxers down his thighs. His trapped knees were pushed up. Dean started when he felt the man’s tongue on him. _“A-Ahh!”_ He squirmed and mewled as the man licked and sucked at his aching clit. He bit his lip when two fingers slid into his cunt, feeling around, searching, until… “Oh, f-f— th-there—” … he found that one spot that, in all honesty, Dean occasionally had trouble finding. Dean thudded his head back against Baby’s hood. Hips gyrating as his fingers tangled in Cas’ hair. The familiar sensations inside this alien body had him dizzy. His brain still couldn’t figure out what to focus on first. He came with a groan, soaking Castiel’s hand, and sagged back on the hood, body trembling.

A glance at the man standing up between his legs showed a smug expression. He’d call him a bastard, but damn. That had been his best orgasm yet.

Cas helped him strip out of his clothes before removing his own. Dean’s body heated up at the sight of the man’s erection. With his normal anatomy, Dean had enough to brag about but… Holy shit. He sat up and drew his knees together. So far, all he’d had inside him were fingers.

“Geez, Cas. You sure it’s gonna fit?”

He chuckled. “Your arousal has allowed your cunt expand to accommodate an erect cock.” He kissed Dean’s temple before taking his hand and pulling him off the hood. “Let’s get a little more comfortable.”

Dean laid out on the Impala’s backseat. He sighed as Cas slowly kissed his way up Dean’s body, his knees on either side of Cas’ waist. He moaned into Castiel’s mouth, tongues warring together. He gasped when the head of Cas’ cock rubbed against him, legs spreading farther to allow the man better access.

“Oh, _fuck_ Cas.” He grasped onto the man’s shoulder, his other hand tangling in his dark hair. He winced a little as the thick cock that slid into him. But, fuck.

Cas sighed. “Dean, you’re so tight.”

“Oh yeah? Am I as tight as _she_ was?” Dean asked, letting his jealousy return as his body adjusted to having Castiel’s cock stretching his virgin cunt.

Cas chuckled. “I’ve already forgotten about her.” His thrusts were slow, experimental. He dropped his forehead to Dean’s shoulder. “Ah, fuck, Dean. You feel so good…”

“Mmm. Yeah, that feels…” _Like exactly what I need._ He sighed, legs wrapping around the man’s waist. “Oh, god Cas. Mmph, yeah. Faster, c’mon.”

Cas moaned incoherently as his hips snapped forward, thrusting harder as he complied. They gasped and muttered each other’s names in between uncoordinated kisses.

Dean braced himself against the door above his head as Cas fucked into him, the now extremely familiar sensation building deep in his core. He changed his mind. He totally was jealous of women’s capacity for multiple orgasms.

_“O-ohh! C-Cas… Ahh, fu-uuck! A-ahh, ah, ah. Fuck fuckfuckfuck— Cas!”_

He didn’t remember being this vocal during sex before.

 _“D-Dean.”_ Cas’ voice sounded absolutely wrecked. “I-I think I’m going to-to—“

“Fuck, yeah. Come for me. C’mon, man. Come inside me.”

Cas pressed his forehead to Dean’s shoulder. _”Dean!”_ With a final thrust, Cas erupted inside him. _Oh my god. Is that…?_ Holy shit. He could actually feel it. _Fuck that’s hot._

They lay gasping, tangled up together. Dean felt his cunt flutter as it contracted around Castiel’s slowly softening cock.

When their heartbeats returned to a more normal pace, Cas pulled back. Dean bit his lips as the now soft cock slipped from his sloppy cunt. His knees drew together, bashful once more as the man’s cum leaked from him. They sat beside each other, not looking at each other, just breathing.

“So, um… what- what I did there… that was correct?”

Dean huffed. “Uh, yeah. Yeah, I’d say that was pretty damn correct.” He grinned and looked at Cas. The grin faded when he saw the uncertain and… _vulnerable_ … expression on the Fallen Angel’s face. “Hey, are you— I mean, was _it_ … good? I-I mean, for _you_. I mean, was that okay?”

Castiel was silent for a moment. He turned to look at Dean. “That was much more than okay.” He searched Dean’s face. “It was… I would…” He blushed and looked away again.

Dean could let it drop. He probably _should_ let it drop. But… “What? You would what? C’mon. Tell me.”

“I would very much enjoy doing… _that_ … again.” He looked back up. “With you.”

A small seed of doubt sprouted in Dean’s mind. Just inside the crack of his defences. “Is…” He cleared his throat. “Is it, y’know, cause of my gender-swapped junk?” he asked carefully. Part of him didn’t want an answer.

“I’m an An— … I _used_ to be an Angel. I am as indifferent to gender as I am sexual orientation. Yes, my… body reacts naturally to the female form, but that is simply because my vessel is, I guess you’d say, ‘preset’ to Jimmy’s original orientation. … However if _you_ are in any way adverse to a repeat of these events—”

“I do. Want to, I mean. Do this, again. With _you_.”

The smile that formed on the man’s — his best friend’s — face made his heart race again.

They pulled on just enough clothing to be decent and snuck to Dean’s room for some naked nap time. Followed by that second round, which was totally _not_ easier on his body than car sex. No, really. He was only thirty-four for fuck sakes.

And Ezekiel can go fuck himself for suggesting, after Dean finally re-emerged, that Castiel had to go. The bunker, as far as they could tell, was warded. And Cas’ new tattoo — which Dean thoroughly admired during that second round — kept him off Heaven’s radar. Dean might be the love ‘em and leave ‘em type when it came to one night stands, but this was Cas they were talking about. He wasn’t going to kick the new-to-humanity-human to the curb after having mind-blowing sex with him. He was an ass, but he wasn’t cruel.

And if he sought out the man immediately afterwards because, the guy was his friend, and an excellent lay, and (dammit) he was horny _again_ … Well, who the fuck cares?

-30-

**Author's Note:**

> Totally ended up with a lot more emotion near the end than originally intended. But they wanted to go there, so I let them.


End file.
